Alastair

Name	Alastair
Actor	Mark Rolston (4.09 & 4.10) Andrew Wheeler (4.15) Christopher Heyerdahl (4.15, 4.16 & 4.21)
Dates	???? - 2009 (killed by Sam Winchester)
Location
Occupation	White-Eyed Demon
Episode(s)	4.09 I Know What You Did Last Summer 4.10 Heaven and Hell 4.15 Death Takes a Holiday 4.16 On the Head of a Pin 4.18 The Monster at the End of This Book (mentioned) 4.20 The Rapture (mentioned) 4.21 When the Levee Breaks (hallucination) 4.22 Lucifer Rising (mentioned) 6.10 Caged Heat (mentioned) 6.20 The Man Who Would Be King (mentioned)

You know the problem with your generation? Instant gratification. It's all now, now, now. No patience, no craftsmanship. But I do have to say... This knife of yours... It's an exquisite piece. You must tell me where you found it. You know... I haven't been up here since Poland '43. Truth is, I loathe it. It's chilly. No stink of blood or sizzle of flesh or the wet flap of flayed skin. I don't know how you stand it. So, the sooner you cooperate, the sooner I can finish up with this ghastly angel business and return home to my studies. But no rush. Let's take our time... Relish the moment. Now, I'm going to remove this, but don't you go smoking out of that meat. You won't get very far. – Alastair, 4.10 Heaven and Hell

History

Alastair is a white-eyed demon whose past is largely unknown but is implied to be quite long. When he was created is unclear, but he considers the centuries-old Ruby to be "young" when compared to himself. He prefers to spend his time in Hell torturing souls, only heading topside when it is absolutely necessary. He claims to be an "old friend" of Death's, who had been imprisoned since Biblical times. Alastair is present for World War II, at which time he is involved with the concentration camps in Poland. He returns to Hell after 1943 and does not resurface on Earth again until 2008. He takes Meg as his apprentice and trains her at some point prior to his demise in 2009.

Alastair is charged with breaking the first of the 66 Seals by forcing "The Righteous Man" to torture other souls in Hell. He first attempts to break this seal by torturing John Winchester's soul from 2006 to 2007, promising to stop only if John agrees to torture other souls. However, John continually refuses the offer and eventually escapes Alastair's clutches through the Devil's Gate. A year later, Alastair receives John's son Dean from Lilith as a replacement for John. Although Alastair expects similar resistance from Dean that he got from John, he succeeds in getting Dean to agree to the offer in a third of the time John resisted it. Once Dean breaks the first seal, this allows the rest of the seals to be broken. Impressed by Dean's potential, Alastair keeps training him as an apprentice until angels rescue Dean.

Alastair is sent to Earth to capture and interrogate Anna Milton on what she hears other angels saying. However, he fails due to the combined efforts of Sam, Dean, Ruby, and Anna herself. He is sent back up to Earth once again to participate in breaking more seals. His attempt to sacrifice two reapers during the winter solstice is thwarted by Sam, Dean, and Castiel, the last of whom captures Alastair to interrogate him on who has been killing members of his angel garrison. Alastair proves too strong-willed for the angels to break and they call Dean in to torture his old tormentor, but to no avail. Alastair only gives up the information when Sam tortures him with his demon blood-enhanced powers; after Alastair reveals that he only knows that no demons are behind the murders, he becomes the first demon killed by Sam's growing powers.

Characteristics

Alastair survives being stabbed with Ruby's knife.

Potestas inferna, me confirma. Potestas inferna, me confirma. Potestas inferna, me confirma! – Alastair, 4.10 Heaven and Hell

Alastair has white eyes (including pupils and irises). He is noted as an expert interrogator and torturer, and is also incredibly resilient to being tortured himself; according to Castiel, he has an exceptionally strong will, allowing him to withstand extended torture from both angels and one of his own apprentices. Alastair possesses an extensive knowledge of the occult as well as Enochian spells and rituals, including an incantation with an unknown negative effect on angels as well as another incantation that expels an angel from his vessel and sends him back to Heaven, and spell-work to incapacitate reapers. His presence causes statues to weep blood.

Powers and abilities

• Telekinetic
• Can possess humans.
• Has high resistance to Ruby's knife.
• Teleportation
• Unaffected by the smiting powers of angels.
• Can overpower angels, though he does not possess the power to kill them.
• Superhuman durability.
• The power to telekinetically inflict damage onto humans's hearts with a gesture.
• Superhuman strength.

Weaknesses

• Can be killed by Sam's powers if Sam has recently consumed demon blood.
• Is unable to perceive an angel's true form without his meatsuit getting obliterated in the process.
• Is vulnerable to devil's traps, holy water, and salt.

Episodes

4.09 I Know What You Did Last Summer

Alastair leaves Hell and possesses a pediatrician to capture and interrogate Anna. He follows Sam and Dean from Anna's house to the church Anna is hiding at. Ruby tries to get Sam, Dean, and Anna to leave as quickly as possible to avoid Alastair, but realizes that it is too late when signs of his approach break out, including a statue of the virgin Mary weeping blood. Although she convinces Sam to exorcise Alastair with his powers, they have little effect on Alastair, who uses telekinesis to fling Sam down the staircase before attacking and overpowering Dean. He taunts Dean about their "closeness" in Hell, prompting Dean to finally recognize Alastair, even in his meatsuit. Sam returns to stab Alastair with Ruby's knife, but much to the Winchesters' horror, the demon does not die. As Alastair pulls the knife out, Sam and Dean flee from him by jumping out the church window and he allows them to escape so that he can use them to lead him to Anna again.

4.10 Heaven and Hell

Ruby tells Sam that Alastair is "practically the Grand Inquisitor" in Hell and that she is more scared of him than even angels. She suggests that Sam resume drinking her blood so that he can exorcise Alastair, but Sam refuses. Later on, Ruby fulfills her part in Sam's plan by letting Alastair find her. Alastair derides her for protecting Anna, an angel, when she is a demon, and rejects her offer to trade him Anna for the safety of herself, Sam, and Dean, instead capturing her and torturing her with her own knife to force her to tell him where Anna is. While torturing her, Alastair reveals that he actually vastly prefers Hell to Earth (which he loathes), having only left it because he must deal with "this nasty angel business." Eventually, Ruby leads him and his minions to Anna; she is unwilling to simply tell him what he wants to know because she knows that he would just kill her afterwards. Alastair and his minions find that Castiel and Uriel are also at the site and are about to execute Anna. Dismissing Castiel's warnings that they will be killed if they do not leave, the demons fight the angels to stop them from killing Anna. Although Alastair's minions are quickly killed by Uriel, Alastair proves too powerful for Castiel to smite and overpowers the angel. When Dean hits him over the head with a crowbar, Alastair shifts his attentions to him and Sam and launches a telekinetic attack on their hearts while chastising Dean about his lost "potential." He tries to intervene when he sees Anna regain her grace, only to get vaporized instead, leaving behind only Ruby's knife. Later, Dean tearfully reveals to Sam that after every day of torture in Hell, Alastair would offer to stop if Dean agreed to torture other souls; although Dean held out for the first thirty years (three months on Earth), he eventually gave in because he couldn't take it anymore and spent the last ten years of his time there (one month on Earth) torturing other souls under Alastair's instruction.

Alastair in his new meatsuit, preparing to break one of the 66 Seals.

4.15 Death Takes a Holiday

Now in a new meatsuit (his previous one having been destroyed by Anna), Alastair is attempting to break one of the 66 Seals by killing two reapers under a solstice moon. He confronts Dean and Sam in a cemetery, and injures Dean, but Sam is resistant to his powers and fights back, revealing that he survived his last encounter with Anna. He flees when Sam tries to exorcise him with his powers and later returns in yet another meatsuit. When the boys become non-corporeal, and therefore subject to ghostly weaknesses, they track Alastair down at a funeral home and he traps them with an iron chain. He kills one reaper, but the boys rescue Tessa, preventing the seal from being broken. Later as he confronts Dean, Alastair is captured by Castiel.

4.16 On the Head of a Pin

Alastair is killed by Sam.

Alastair is captured by Castiel and Uriel and imprisoned in a devil's trap, but he refuses to tell them anything about the slain angels. Dean is recruited as an interrogator because he was formerly Alastair's student during his time in Hell. After extensive torture, Alastair breaks free Uriel having sabotaged the devil's trap to prevent his role in the angelic deaths being revealed. He almost kills Dean, but is stopped by Castiel, who throws Ruby's knife and embeds it in Alastair's chest. Alastair pulls the knife out and fights Castiel. He manages to trap him against a pillar, and admits that while he is unable to kill the angel, he will send him back to Heaven. Alastair begins to chant, but he is stopped by Sam, who has become strong enough to overpower him with ease. Sam forces Alastair to talk, then kills him via his abilities.

4.18 The Monster at the End of This Book

Dean reveals that Castiel has told him about Sam torturing and killing Alastair with ease. Dean thinks that this is one of the signs that Sam is going dark-side.

4.20 The Rapture

Dean points out that Sam's powers used to be strong enough to kill Alastair but are now not even strong enough to kill a low-level demon.

4.21 When the Levee Breaks

While undergoing forced withdrawal from demon blood, Sam has several hallucinations, the first of which is Alastair inexplicably returning. Sam hallucinates that he is strapped down and tortured by Alastair with a knife, but eventually Alastair disappears and Sam realizes that he is hallucinating.

4.22 Lucifer Rising

Ruby reveals that not even Alastair had known that she was working undercover for Lucifer and Lilith.

6.10 Caged Heat

To prove that she is capable of making Crowley give into her demands, Meg reveals that she had apprenticed under Alastair in Hell like Dean had, and Dean grudgingly concedes that this means she can make Crowley do whatever she wants. Meg doesn't reveal when she undertook this apprenticeship, but it must have been before Alastair's capture in 4.15 Death Takes a Holiday, as he was killed in the following episode.

6.20 The Man Who Would Be King

Crowley mentions Alastair when listing off those who underestimated the threat the Winchesters pose and paid the price for it.

Alastair in Lore

The character Alastair may be a reference to the demon Alastor in Christian demonology. Alastor is the chief executioner and torturer for the monarch of Hell. He is an exceptionally cruel demon. The name "Alastor" became a common place term in reference to evil spirits or foul tempered individuals.

Trivia

• The name "Alastair" is the anglicized form of the Scottish Alasdair, which is the Scottish (Gaelic) version of Alexander. The latter is the English form of the ancient Greek name Alexandros, which has the meaning "protector of men" in Greek.
• The character may be a reference to British occultist Aleister Crowley, who during his day was dubbed "the wickedest man in the world" by the press. At one point, Led Zeppelin guitarist Jimmy Page developed an interest in Crowley. Page once owned Boleskine House, Crowley's estate on the shores of Loch Ness.
  • In addition, another demon named Crowley later appears.

External links

• Interview with Mark Rolston